From Basketball To Entrepreneurship With Dre Baldwin

Dre Baldwin, the Founder of Work On Your Game, Inc., is an influencer who has millions of views on his YouTube channel. In this episode, Dre joins Dr. Diane Hamilton to share his journey from basketball to entrepreneurship. How did he switch from being a pro basketball player to having 73+ million reach through various platforms? You’ll be surprised to discover that the principles of success you apply when playing basketball are the same in every other area of your life! Want to learn some of the principles that Dre uses in his own career? Tune in to find out!

TTL 806 | Basketball To Entrepreneurship


I’m glad you joined us because we have Dre Baldwin here. Dre is an entrepreneur, keynote speaker, author and ex-professional athlete. He’s a huge influencer on YouTube and so much more.

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From Basketball To Entrepreneurship With Dre Baldwin

I am here with Dre Baldwin, who is an entrepreneur, keynote speaker, author and ex-professional athlete. He has done many things. I don’t even know where to go with you, Dre, so I’m just going to welcome you to the show.

What’s going on, Dr. Diane? I am doing excellent here. Thank you for having me on.

You’re welcome. I am excited to talk to you about what you’re working on. I know that you’ve got an interesting background. My brother was a basketball player. I’m the shortest one in my family. I’m 5’8″. They don’t know what happened to me. He’s almost 6’8″ and my sister is 6’3″. They’re thinking I’m little. I’d like to get a little background on you. How did you get to this place in your career?

Where did your brother play basketball?

He played at ASU, Arizona State University.

I’m wondering if I know him. I don’t know what year he played.

He’s way older. I’d like to get a little background on you. How did you get into basketball? You were professional basketball. You played college basketball. What you’re doing now, I know you do a lot of different things. You have all these TED Talks. You’ve authored 27 books or something like that. I was like, “Wow.” I wanted to see how you got to this level of success, just a backstory.

I was always into sports, Diane. I played all the sports that kids play growing up. That was the thing that I spent my time doing. I might be a generation after you, but I was still in the era before we had smartphones. Maybe we have video games, but we mostly played outside. I played football and a little bit of baseball. Finally, I got to basketball around the age of fourteen, which was pretty late for a player who wants to advance and who is ambitious in any sport. Nowadays, you’ve got kids and their parents are getting them trainers when they’re eight years old. I’m fourteen just starting to play basketball. I didn’t have any trainers. Nobody took me under their wing. Nobody in my family was a basketball player either. I’m the one who got lucky in the opposite way. My parents are not even tall, but I am 6’4″ and they are not even 6 feet.

I started playing basketball. I didn’t make my high school team until I was a senior. We didn’t have JV and a freshman team. That was just one team. If you didn’t make that team, you don’t play. I didn’t make it until I was a senior. I sat on that bench. That year, I didn’t play. I averaged about two points a game, even though I did have a jersey. I had a front-row seat to all the games. I walked on in college. I played at the Division-3 level of college basketball. Your brother probably played at Division-1. Most D-3 athletes are not the ones who become pros. The D-1 athletes become pros. It was far-fetched to me even thinking about becoming a pro athlete, but I had this idea that I could. Being a late bloomer in the sport and started playing late, my development was a little bit behind the average player who starts to play earlier. I felt like I still have more room to grow, so I kept trying.

By the age of 23, this was the year removed from graduating from college. I worked in a couple of “regular jobs” after I graduated college, then I went to this event called an Exposure Camp. This is something that if you’re not deep in the sports world, you probably don’t know what that is. The Exposure Camp is a job fair. Instead of you showing up and telling people what you can do, and handing them a paper resume, you bring your sneakers and shorts, and you play that sport in front of an audience of decision-makers. These are coaches, agents, scouts, managers, people from around the world who are looking for talent. It’s like a casting call, but you’re performing in front of them.

The challenge with a basketball exposure then is that basketball is a team sport, but everybody on your team at the event are all trying to make themselves look good. It is a paradox there where everyone is trying to make themselves look good, but you’re supposed to be playing a team sport at the same time. Everyone is trying to be the star at the same time. It’s tough. There was a balance you’ve got to strike there. Luckily, I was able to strike that balance and I play well there. I got the scouting report and the footage from that Exposure Camp. I went and sold myself to some agents. I need to get myself an agent. The way the agents work in the basketball world is the same way they worked in the acting world or the literary world. The agent is the go-between between the job opportunities and the talent who wants the job. I got an agent. That agent is the one who helped me start playing overseas.

You played overseas and you ended up getting back into the business world. You’re giving talks. You’re doing other things. I’m curious where that led. How did you get to that?

It’s a ten-year jump. I’ll tell it quickly. I started playing professional basketball in 2005. I published a video. It was the footage from that Exposure Camp. It was some highlights from that. I’d put it on this brand-new website that not many people knew about. It was called I wasn’t thinking it was going to be anything. There was nothing to gain from putting videos on the internet in 2005. I put it up there. It was just for me because the footage that I had was on this thing called a VHS tape. If you have Millennials in your audience, they can google it and look it up, or ask their parents. They’ll come up on what it was.

If you lose the VHS tape, if you drop it, it gets wet, or you left it in the sun too long, your footage is gone. I’m thinking, “I need this footage for the rest of my life. It’s the most important basketball footage I own.” I wanted to put it somewhere where it would last. That’s why I had it transfer it to a data CD and put it on YouTube. I forgot about it. I’m playing ball overseas. I’m in Lithuania, Mexico, traveling in United States, Germany, Montenegro, playing ball. I would put videos on YouTube sporadically. Every now and then, I would put a video up there because I thought that players were responding to this. What had happened when I put that first video up, months later, I went and looked at it and there were comments on the video. I don’t know these people and I know they don’t know me, but they’re asking questions like, “Who taught you how to play basketball? How often do you practice? Can you make a video about shooting? Can you make one about dunking?”

[bctt tweet=”Get some skills in what you enjoy and love doing. ” username=””]

The light bulb went off in my head and I realized that this was an underserved audience. There were a bunch of people who wanted to learn basketball, but there was no one to teach them. These kids who were asking me these questions were me ten years ago. They’re the same player that I was. I didn’t have anyone to teach me. They needed someone. The advantage that they had was that they could go to the internet and ask for help. Whereas our generation, there was no internet to go to. Internet existed, but it was nothing like it was even in 2005. They could go and crowdsource knowledge where we were stuck with whoever you know. If you don’t know anybody, then you’re stuck with nothing.

I started making more videos to show players how I practice. I was going to the gym every day anyway. I was slowly getting a little bit of an audience on YouTube, but who cares? If anybody remembers the internet back in 2008, 2009, if you’re blogging or making YouTube videos, you’re a loser. You’re a bum living in your mom’s basement. It’s like, “When are you going to get a real job? You’re making videos and blogging.” That was nothing back then. People were like, “Go take a shower and shave.” Around that time, I found myself unemployed. I didn’t have a job in basketball. In professional sports, sometimes you’re a free agent. You don’t have a team that signs you because everybody can’t get a job in professional sports. There’s a limited number of teams and roster spot.

At this point, I have a little bit of an audience on the internet. At the same time, I didn’t have a job playing basketball. I was like, “If I project my life out 5, 10 years from now, I don’t have control over my destiny.” I asked myself an important question. It’s probably the most important question I’ve ever asked myself. The question was this, how can I take the thing that I loved doing, which was basketball, and something I’m good at? I always loved being on computers and the internet and then, how can I make money from it?” I was in a little intersection of three things, what I’m good at, what I enjoy, and making money. The answer to that question became what is now the which was a website I had at that time. This is my personal website, then it was the Work On Your Game, the brand and philosophy that we have.

It’s at the exact same time that this social media start. We were just starting to use that phrase. This content started to get monetized. It starts to be a thing where you can make money from putting stuff on the internet for free. Before that, if you were putting stuff on the internet for free, it was like, “When are you going to get serious and do something with your life?” Now, it became a thing. I’m like, “I can make money from this.” I started creating my own products. I’m not talking about any high-ticket masterminds. I’m talking about $4.99 training programs that I’m selling to 13 to 21-year-olds. We fill those things at volume because I had such an audience on YouTube for making these basketball videos and I knew who my audience was. I knew I couldn’t sell them a $5,000 coaching program. They don’t have that kind of money, but anybody has $5. We’re selling thousands of these programs through YouTube. No advertising, no nothing. It’s just telling people about it in our videos, and people are coming to buy our products.

When I first started selling those products at $4 or $5, that planted a seed in my mind. I could do this for the rest of my life. I won’t be able to dunk a basketball forever, but I can use my brain. I can sell my intellectual property forever. This was around 2009, 2010 that that started. Fast forward to maybe about a year later, players were asking me about my background because they found out about this, “You only played one year at high school. You walked on at a D-3 college, and then you still played overseas?” The thing that I tell people all the time about my background in basketball is, “When you watch TV basketball, you see Michael Jordan, Kobe, or LeBron James. Every one LeBron James, there are thousands of Dre Baldwin.” Most basketball players do not have LeBron’s background. They are the blue-chip star. They were not kissed by God when they were born. They hit the genetic lottery.

I had the genetic lottery. I’m 6’4″, I have long arms, and I can jump high. I hit the Pick-6. LeBron hit the Powerball. Most athletes are not at LeBron’s caliber. They do not have that kind of background. They saw me and they saw hope. They said, “I got cut from my high school team. I am playing at a junior college. I don’t have any scholarship offers, either. Maybe I could do it. If this guy or this random dude who I’d never heard of on the internet did it, I can do it.” They saw hope in me. That lead to players who are asking me more about my background. That’s when I wrote my first book, I called it Buy A Game, which was a piece of advice one of my middle school teammates had given me. Buy a game, meaning get some skills. It’s a euphemism. That was my first book. After I did that, they printed the book in my mind because I’ve always loved writing. I’ve always been big on reading and writing. My mom is an educator so I was always big into that. Once I saw the opportunity to self-publish, I said, “I’ll write another one.” I wrote another one and another one, and here we are to this day.

The stuff that I was talking about was the same things that these players were always asking. They were asking me, “How do you dribble, shoot, and dunk?” The technical and physical skills, but a lot of times, the players were asking me things like, “Why do you come to the gym every day to work out? What motivates you to do it when you don’t always have the success or didn’t always have it? How can you perform in front of an audience the same way you perform when nobody is watching?” People with performance anxiety or nerves. “Dre, since you got cut from your high school team all those years, what was it that gave you the idea to keep trying? You played at D-3 college ball. Most D-3 athletes are not even thinking about becoming a pro, but you went after it. You’ve invested in yourself to do it. How did you even have the mentality to think that it was even possible, let alone go try it?”

It was clear to me and I thought this was a normal thing because this is the way that I think. When I realized through the questions I was being asked that most people didn’t think like this, I started talking about this stuff. I found out that what more people wanted from me is the mindset stuff than they wanted the actual basketball stuff. That’s how I started talking about the mental game, and because I was talking about it, I started doing these videos every Monday. I called it the Weekly Motivation because about this point, once I saw that you could make ad revenue from putting videos on YouTube, I said, “I’ll put a video up every day.” I have 8,000 videos on YouTube to this very day. The majority of them, still to this day, were from the basketball days. There was a point I was putting up 4 or 5 videos a day because that’s how much the audience wanted it.

Once I had all these videos up and I saw the people were asking about the mindset stuff, people who were not athletes started finding my stuff. They were saying, “Dre, I’m not trying to learn how to play basketball, but I still subscribed to you because that one video you put out every Monday where you talk about mindset, that stuff applies to everybody and anybody.” That told me what I could do when I was done playing ball. I hope people are paying attention to these dots that got connected. It was great that I graduated college at the exact time that what we have now was just beginning. I was the first to market when it came to putting athlete workouts on the internet. I noticed these things. I also had to take advantage of it.

When I noticed that people who weren’t athletes were not seeing my stuff, I realized and I always knew that athletic careers are pretty short. The average basketball, baseball, football, hockey career is less than five years, all of them. I knew, at some point, I’m going to have to find another way to give value to the universe that has something to do when I wake up in the morning besides playing basketball. I already knew what it was. This is while I’m still playing. I was only halfway through my career when this happened. I said, “When I’m done playing ball, I’m going to take this mindset stuff. I’ll do it full-time.” In 2015, when I stopped playing, I was already selling programs. I was making my own products while I’m playing basketball overseas.

When I stopped playing in 2015, I already had that going. I could make it more professional, put some structure to it, and understand how to run a business, which I didn’t know back then. I thought I did, but I didn’t. I started to learn that once I stopped playing ball. Fast forward to now, Work On Your Game Inc. is the company, and what we do is we take the mental tools to get you to the top 1% of the sports world. We translate how those tools apply in the work world, in everyday life, and to the individual out there who is trying to figure out their way, or they know their way, but they’re having some challenges getting to it.

We covered so much. I’m interested because I know you mentioned how many videos you had. At one point, I saw your subscribers were 134,000-plus at the time that I looked. You had 73 million views and different things of all your content. You have done a lot. You have a podcast. Is it called Masterclass? Is that the name of your podcast?

The podcast is called Work On Your Game, but I call it a masterclass. I want to be categorized as a podcast.

You had 1,500 episodes. After my 800, I was starting to get a little bit like, “Look at him.” That is crazy. Three million downloads. I’m looking at some of your stats. From my perspective, I know how tough that is. Giving four TED Talks, most people freak out giving one. How hard was that for you to give a TED Talk?

TTL 806 | Basketball To Entrepreneurship
Basketball To Entrepreneurship: Athletic careers are pretty short. The average basketball, baseball, football, or hockey career is less than five years.


It wasn’t hard at all.

Everybody tells me it stresses them out. You didn’t get stressed at all from that?

Not at all. Maybe we are similar in this and that. I like public speaking and being on stage. I get excited when I get an opportunity to speak. Like this conversation, this is public speaking, even though we can’t see the audience. It doesn’t stress me out, but I understand how others can be stressed out by it.

When you talk about Work On Your Game, your show, are you dealing with just athletes, or is this for the everyday person to be able to figure out things and better themselves in life?

Work On Your Game is not just for athletes. We take the four principles. Our business is centered on four tenets. Discipline, showing up every day, do the work. Confidence, put yourself out there boldly and authentically. Mental toughness, keep showing up, doing the work, putting yourself out there, even when the success you have expected to achieve is yet to be achieved. Personal initiative, making things happen instead of waiting for things to happen. Anyone who reads this, nobody can tell me that they haven’t needed each of those four principles to get to where they’re at right now in life. I don’t care if you’ve never played a sport ever.

It’s interesting because I’m a curiosity expert and I researched what keeps people from being curious. I’ve had many people on the show talking about curiosity, and how it ties into so many things in terms of motivation, drives, success, everything that you could think of that curiosity was the spark to it. Where does curiosity fit into your four pillars?

It fits into confidence and having the belief that if you ask yourself a question that you haven’t been asked before, and being willing to dance with that question. A lot of times, people get so stuck in a rut. They only want to look at the things that they know. They only want to do what they know. They only want to talk about the things they know. If you ask them a question that they haven’t been asked before, they bristle at the idea of the question. They don’t want to even explore what answer might come from it. I’m sure you’ve seen that in your practice.

That’s interesting because what I was looking at is, what keeps people like that? Why do they go in a different direction? Why don’t they ask questions? What keeps people from asking and providing content and information to people? I found four things. It’s fear. It’s the thing that they tell themselves, their assumptions. It’s technology, the over and under-utilization of it. It’s their environment. Everybody around them says, “This is cool or isn’t cool. You should do this or shouldn’t do that,” and that type of thing. It fits into all of your areas as you talk about it. To be disciplined, you have to have that desire to want to do something. That takes the curiosity to move that way. It ties into confidence. It ties into all of the things that you were talking about, mental toughness, personal initiative. For me, it does. I look at curiosity as the spark. That’s something that I hope you talk about on your show. It’s fascinating to talk about what keeps people from being curious.

I don’t think they recognize those four factors are holding them back of what they tell themselves, of who’s put that thought in their head. It could be their parents said, “You should always do this or that. It’s a dumb thing to do according to your siblings.” All the stuff that we get and all this mind clutter and chatter. What you talked about is important because confidence is important. No matter if you go into sports or whatever you do, you have to have that sense that what you say matters. I was very interested in your books. I noticed in The Mirror of Motivation, you’re talking about keeping goals in your mind, preparing and finishing strong, and all of the things that we talked about. You also deal with haters and naysayers. That’s a big part of what holds people back when you have these voices telling you. That’s tough. When you’re on YouTube, you must have gotten a lot of nasty, snarky people because you get those kinds of people on these sites. Did you have to deal with that much?

I want to unpack everything that you said. When it comes to curiosity, as you said, the discipline is to even be willing to ask the question. Confidence, believing that whatever the question is and the answer that comes from it, you can handle it. Mental toughness is to dance with that question, even if the question is challenging to you and it challenges some of your preconceived beliefs. The personal initiative is to even try it like, “Ask me some questions that I haven’t been asked before. Let’s see what comes from it.” You’re right. It’s funny when you said that. In all the episodes of my show, I don’t think I’ve ever used the word curiosity in the title. I don’t think I ever had. However, I do have episodes where that was about asking the right question. That plays a huge role in curiosity.

This is why you find mentors, coaches, you take courses and read books because another person will be able to ask you a different question. We get into these zones mentally where we think the same way. We go through these same patterns all the time. I’m like, “When everybody walks through the grass the same way, it’s off the beaten path through the grass, but nobody walks through the rest of the grass that’s why it’s perfect.” It’s the same thing in our minds. It’s being willing to ask yourself or being willing to let someone else ask you the right question. What I tell people is that an expert, a doctor, a coach, a mentor, or a speaker, their job is not to give you the answers because Google has all the answers. Their job is to help you identify the right question. If you ask the wrong question, Google will give you the answer, but it’s not going to help you get anywhere. That right question is the thing.

Going to your question that you asked me, it might be called MediaTube. It’s something that I have integrated with my YouTube channel. In WordPress and sites like that, they give you your year-in-review. They tell you how much you did this, or listen to that or whatever. MediaTube sent me an email and they said, “In the year 2020, I responded to 220,000 comments on my YouTube channel.” To answer your question, did I receive any nasty comments? Yes.

How do you respond to them?

It depends on the topic. You get more or less, depending on what you’re talking about. If I talk about basketball, it’s bland. Different topics, especially in 2020 with the stuff going on, I talk about anything and everything. How do I respond to them? It depends on what people say. Like if somebody comes in and they’re in the trolling area where they’re saying anything just to say it, I get rid of them. What I’ve found in the comment sections on the internet is that people are cheap. If they see a whole bunch of negative comments, then they’ll be negative. If they see a whole bunch of positive comments, then they’ll be positive. If I see people being negative, then I get rid of the negative people because they won’t influence more people to be negative. I’ve found that is true. That’s how it works on the internet. I’ve probably responded to 2 or 3 million comments over the last fifteen years so I’m now qualified to say it.

[bctt tweet=”Put yourself out there boldly and authentically.” username=””]

That takes a lot of time to do all that. On LinkedIn, I’m close to maxing out of what you can have people following you there. Before, they just have to follow you. I should say connections. You get tagged on a lot of things, whether you’re even part of it or not. How do you keep up with being tagged on everything and being listed on everything? Do you look at everything where you’re listed?

Do you mean on LinkedIn?

Yes, even on LinkedIn. I don’t know how it is on YouTube. Can they tag you? I don’t even know if they can on YouTube. Do you get tagged a lot?

I don’t think they can tag you on YouTube. They can in a comment. Somebody could make a comment and maybe you could tag your friend and say, “You should check this out.” I don’t get too many of those. I don’t get too many people tagging me of other people’s stuff. I don’t pay a lot of attention to other people’s stuff. I just do my stuff and let people come to talk to me. People respond to my comments. The reason I’ve always read my comments is because I’m a creator. I got the idea for making those basketball programs because somebody in a comment said, “How about you do this?” That’s where I got the idea from. 

Have you done anything on Clubhouse yet? Are you familiar with Clubhouse, the new app?

Yes, and yes. I did a room with my friend, Patricia. She’s a writer. She helps people write their books. We were talking about book publishing. We do that every week and I’m doing another one now.

How was it?

I love Clubhouse because of the immediacy and simplicity of it. There’s no way to game the Clubhouse. People are trying, but there are not as many ways to game the system on Clubhouse as there are on every other app. That’s what I like about it.

Are you monetizing your time on there? They don’t have ads. Now, it’s in beta and all that, but you can have your websites, “Come find me,” kind of thing. What advice are you offering? The few Clubhouse things I’ve attended were helpful, but it’s a lot going on. Since you were early to YouTube, I figured you’d be early to that. How do you know which one is the next one to be early to? What do you think is going to be the next big YouTube-ish sensation?

Firstly, I’ll clarify something I said. I think I said 200,000 comments, it’s 21,000 comments. I’m not as a hard worker as I thought I was. You can’t charge people on Clubhouse, so you cannot get paid from Clubhouse, the same way you can get paid for having a podcast. You can monetize it by connecting. They get the value from you, they see that you’re good, and then you move into the next step. It’s the same way you can do with your show. Have you used Clubhouse?

Yes. I’ve had some friend-type of conversations. I’ve listened to other conversations. It seems like you proved you’re an expert to people. You give advice and different things. You can learn about different things. What have you used for?

All the different things that I talk about. I’ve got an eclectic group of friends. I’ve got friends who are basketball agents because I play basketball. I’ve got friends who are book writers and book publishers. That’s the main thing that they do because I’ve written books. I’m doing one at 3:00 with my friend. She coaches athletes on their mental health. Since I talk about mental toughness, it’s a great combination between the two of us. We’re going to be talking about that. I talk about different topics. I have my own club, Work On Your Game, where I can talk about whatever I want. I’ve got another club for overseas basketball. I’ll be talking about that as well.

To answer your original question about Clubhouse, about what’s the next thing and how do I know, on Clubhouse, you give value and say whatever you’re saying. There’s nothing you can do on there. There are no messages or anything like that. People will follow you on your connected account like Instagram. Most of the time, it’s Instagram. Anybody who wants to increase their Instagram following, all you had to do is get on Clubhouse, get in rooms and talk, and people will follow your Instagram. That’s the only thing they can do to follow up with you because they can message you on Instagram. I do rooms on there. I’ll give them value and people come to follow me. Now, they’re in my ecosystem. They’ll see what I talk about and what I’m about. They’ll come to get my book. They can come to get into my funnels and whatever is going to be.

To answer your other question about, how do you know what’s going to be the next thing? How do you know whether to invest in it? I see what people are saying. I look at friends of mine who are trusted, who know what they’re doing. They can tell me what they’re getting out of it. They can let me know. It was my friend, Bonnie. She coaches women entrepreneurs. That’s her. She knows her avatar perfectly. She does two Clubhouse rooms a day and targeted women entrepreneurs. I still come in and listen to her rooms, even though they’re targeted at women because she’s good. She’s the one who told me like, “Clubhouse is the thing to do and I’ll monetize it.” She fills up her programs through doing Clubhouse rooms.

TTL 806 | Basketball To Entrepreneurship
The Mirror Of Motivation

What’s her name? I’ll look for her on there.

Her name is Bonnie Frank. She has a room called the Business Fabulous Academy for women entrepreneurs. You’ll find her easily because she’s very active. She might be doing a room right now. That’s how active she is. Tell her I sent you.

I will do that. Do you do TikTok or not?

That’s the only one I don’t use. Everything else, I use.

It’s a little different crowd of what you’re trying to reach. You want to be where your customers are. Since I’ve taught so much marketing and different business courses running, I’m a dean and I’ve been MBA Program Chair in all these different positions. You look at how to reach people with your content. To have the shotgun approach, you have to be focused. Do you talk about helping people get more focused in their lives?

Yes, people usually come to me asking about that. My area of focus, if I had to narrow it down to one thing, it’s mental stuff. Under the umbrella of mental toughness, you have discipline, confidence, getting started, dealing with setbacks. You have, “Let me get more strategic about what I’m doing in my business. Let me become more focused.” People will come to me. They get curious and they want to know, “What does this guy talk about?” I’m looking at your website right now. I will assume there’s potential. People get curious, “How can you help me on my potential?” They probably want to sample the product a little bit, and then you have a show. You have a radio show so people can listen and they can get a feel, “Now, I see what she’s about. This is for me, or this is not for me.” They can come in deeper or they can find somebody else.

Since I do so much assessments, training and speaking, I know you speak and do different things. Do you go to organizations to consult? Do you stick mostly to online presentations? What’s your main focus?

I like doing both. I’ll answer a different question and I’ll say it like this. Let’s say someone said, “Dre, you can only do one for the rest of your life. You can never do the other one ever again.” I would focus on in-house my own ecosystem, bringing people into my funnels, building my list, and selling directly that way. If I could only do one thing, I would do that.

You’ve appeared in national campaigns with Nike, Finish Line, Wendy’s, Gatorade, Buick, Wilson Sports, Stash Investments, and Dime Magazine. When you say you’ve appeared in these national campaigns, in what respect?

Some of those were advertisements where I was the model. Some of them were brand influencer campaigns where we did a whole campaign. For example, Finish Line did a campaign once called The Fundamentals. They were getting immersed in the basketball world. They brought out a bunch of basketball influencers. I was one of them. We did a whole shoot, and they put all this gear on us. We got to keep the gear. That was fun. We were playing basketball. They were taking photos and videos. They give us all this stuff, and then we’re in these campaigns. If you went to a Finish Line sneaker store in 2015, you would have seen a picture of me on one of those little rollout billboards they have in window advertisements. I’ve been on billboards.

Somebody in Africa once sent me a picture because I did a photoshoot with a guy who sells the royalty images, where you licensed the image, and I was the model for some of his shots. I’m from Philadelphia but I live in Miami. I had people I went to high school with in Philly sending me pictures on Facebook of me on the side of a public transportation bus and a credit card company because I was doing the shoot. I’ve been in people’s textbooks. There was this one guy who was on these licensing images world. I didn’t even know that until after the shoot when my photos started popping up on razors. People are in the malls buying razors. My picture is on the box, all kinds of stuff.

As an influencer, I’m curious if you bought at GameStop or what do you think of that whole thing?

No, I didn’t. By the time I heard about it and then started learning about it, they were already shutting it down and everything. The price is going up.

That was a crazy story, wasn’t it?

It was, at least as much as I read about it. I didn’t get too deep into it.

It’s interesting to see the impact that an influencer can have. Just because you have many followers, you have many people who listen to what you have to say, that it would have an impact on stocks and different things. It’s a new time. I never heard of a story quite like that one. You always think that there are other things that control the stocks and that couldn’t happen, a stock running up and then crashing down just because influencers are talking about it. It’s an interesting position to be in as an influencer. I know a lot of people contact me to do things because they see me on this or that or whatever. Do you get overwhelmed by the number of people who want to have you promote whatever they’re working on?

[bctt tweet=”Keep showing up and doing the work even when the success you have expected to achieve is yet to be achieved.” username=””]

As far as now, not as much. Originally, how people came to know me was through playing basketball. I’m not posting videos of me playing basketball because I don’t play anymore. I’ve reinvented myself more into the thought leadership, mental game world. It’s the whole new wave of basketball players who do that stuff nowadays. I don’t have that problem if you want to call it that.

I’ve had a lot of former football, NFL, and different people on the show who’ve done different things. A lot of them have got into speaking and sharing what they’ve learned from being a professional athlete. I was raised in a hypercompetitive family. My dad would probably have been fine if I tripped the guy next to me to win or whatever. It was like, “Whatever it took to win.” We all went into sales, and we’re all super competitive. A lot of people don’t have that discipline and mental toughness that comes from the competition as a kid. How much did sports influence your ability to have those traits? Did those traits put you into sports?

No, the first one. It was a combination of both. I don’t think it was one before the other. I always played sports. When I started playing, I realized that I was more competitive than most of the other people playing. I don’t know which one came first. It came at the same time as I just do.

A lot of people don’t want that competitive mindset. Now, things are a lot more teamwork. When I was a pharmaceutical rep, I was all alone in my territory. Later they go, “If one person is calling on this doctor, it gets you this much sales, then two would be even better.” You’d have a two-person team. They then go, “Two was good. Let’s have four,” then four was good. By the time I left, there were eight people calling this poor guy in a four-week period or whatever. You had to work on these teams. We were all super competitive, but yet we had to work as a team. How much do you deal with that when you’re talking to people about teamwork, cooperation, and that type of thing?

People don’t usually call me for teamwork, honestly. Mine has always been about personal leadership, personal development. What do you need to do yourself? With teamwork, every once in a while, somebody may ask me a question or two about it, but my focus has always been on what does each individual person on this team needs to do to be the best version of yourself, and leadership is a part of that, but we’ve got to get number one right first.

That’s such an important thing too. You talk about believing in yourself more than you believe in anyone else. A lot of us compare ourselves to other people. For me, my competitive spirit is more of, what was I able to do in the past? What can I do now? I compete with my own past successes. When you were talking about mentorship before, I serve on a lot of boards and one of them is a global mentorship network. Mentoring is going to be the hugest thing we see because everybody is trying to reinvent the wheel. It’s already been invented. How do you know who to go to for mentorship?

One thing that I tell people these days with many potential mentors/experts out there, some of them good, some of them not, it’s narrowing down and choosing your mentors. You can’t listen to everybody. It’s impossible. It’s too many people and not all of them are even good. If you listen to too many, their ideas and techniques are going to start clashing against each other. Two people could both achieve the same success but do it in two completely different ways. How do you know which one? For me, I choose no more than 3 to 5 mentors. I tell people, “You find one expert in whatever areas matter to you. You focus on their stuff and consume everything they ever put out. If they’re selling something, you buy it. If they have an event, you go to it. If they have some free content, listen to it, read it, watch it. That’s it. Take in everything that they say and do it, and focus on those people.”

It’s a good thing to find who works for you. When I was a pharmaceutical rep, they used to have us do days in the field before we were hired to see what it was like to do the job. They didn’t just have us ride with one person. They had us ride with 3 or 4 different people so you get a different perspective of how they each did the job. Had I hooked at the first person, I would have never wanted to do that job because of the way she did it. It did not align with how I think. I am a super-efficient kind of person. She was putzing around doing all this stuff. I’m thinking, “Is this how I have to do this?” I watched the next person and I’m like, “That works. That makes much more sense.”

Sometimes you have to be able to find the people who align with what you have and what you think. It’s tough. When I wrote my dissertation, I wrote it on emotional intelligence. I think that emotional intelligence, I’d look at sales performance based on that research. We get hired for our knowledge, and we get fired for our behaviors. Emotional intelligence is a big factor of what makes people unsuccessful. How much do you deal with things like soft skills, emotional intelligence, and that type of thing?

It’s a lot. This whole conversation, a lot of what we’re talking about here are all soft skills. Everything we talk about in Work On Your Game are discipline, confidence, mental toughness. You can’t hold those in your hand. Those are skills. They’re not what we traditionally mentioned as soft skills, but they’re hard soft skills.

How do you train that though? I guess it was a better way for me to word it. It’s hard to quantify some of that. I quantified it in my Perception Index of how we perceive things and I quantified the curiosity. Some of this stuff, how do you know if you’re disciplined enough? How do you know if you have enough initiative?

One of the main things is you have to know what your outcomes are. What is it that you want? It can’t always be about comparing yourself to other people. There will always be somebody who is better than you, and there will always be people who are worse than you. If you’re always measuring by other people, you’ll always be chasing your tail. What is it that you want to achieve? What is your enough? This is an important question for people, especially these days where it seems like everything is unlimited, “Let me get more followers. Let me make more money because this guy seems to have made ten times more than me. Let me get on another social media app. Let me do another live stream.” It was always more and more. The algorithms of the applications are based on that to keep you on them. That’s how they make their money.

It’s asking yourself, what is it that I want? When do I know I’ve reached the outcomes so I can stop, or at least stop for the day? I’m sure in your business, you have clients who will say stuff like, “It’s hard for me to take a day off or spend time with my kids or my significant other because I always feel like I could be more productive.” Everybody is chasing productivity because they don’t know what their enough is. They don’t know when to stop. Even on a daily level, what do you need to get done now? If you could ask a lot of entrepreneurs, what do you need to do now that you can say your work was completed? They don’t have an answer because they don’t even have a strategy. They don’t even have a system in place for knowing what they need to do right now, this week, this month, this quarter. They’re just doing stuff and hoping this stuff works. I used to be that person. Luckily, I solved that problem by putting some structure into my business to where I know when I can stop.

The structure is critical. I’m a big calendar person. I keep a lot of things tracked. The day has got to stop somewhere. When you’re talking about looking at people being better than you, you want to have people around you who have done more or are higher achievers in some respects so you have something to learn. A lot of people want to be the smartest, the best in the room, but that would be very boring. You don’t know what you don’t know unless you’re around people who know a little bit more. Do you advise people to surround themselves with people who maybe have a little bit more going on?

TTL 806 | Basketball To Entrepreneurship
Basketball To Entrepreneurship: In professional sports, sometimes you’re a free agent. You don’t have a team that signs you because everybody can’t get a job in professional sports.


Yes. I’m a part of mastermind groups and joint programs. I want to be around people who are smarter than me, I can soak up the game from other people. At the same time, you have to be able to add something so that’s the balance. The balance is you want people who are better than you, smarter than you, can do things that you can’t do, have seen what you haven’t seen. At the same time, you need to bring something to the table. You can’t come to a potluck empty-handed. You have to bring something to put out some food on the table.

My job is to keep working on my game so I have something to offer people, while at the same time, knowing when to shut up and listen to the people who have done more than I have in certain areas. A good way of doing it is finding people who have strengths in areas that are not yours. For example, in one group, there’s a guy who does his whole businesses speaking gigs. When he meets somebody like me, I can ask him how he books his speaking gigs. I do speaking gigs, but that’s not my main focus. He’s looking at me like, “Damn, you’re doing all this digital marketing stuff.” He doesn’t even know how to build a funnel. I can help him so we can help each other. It was a symbiotic relationship.

You had the foresight to see that YouTube was going to be something. A lot of people probably would love to have a huge following on YouTube. I know a lot of people try to do that on Twitter or whatever. If you don’t get in at the beginning, it takes a lot longer now at this point to do the same growth. What advice do you give to people who didn’t get in early?

Go somewhere and give value. Even though I was early on YouTube, it was a stroke of luck. I’m 23 years old and just starting my pro basketball career when YouTube came out. I didn’t plan that. It just happened. At the same time, it’s 2021 and I’m still doing YouTube. I’m still putting videos on YouTube on a consistent basis. I’m not a sprinter. I’m a distance runner. I mean that literally and metaphorically. I play the long run. I’ve never had a piece of content that goes viral. All those stats that I put out there in front of me are impressive, but I’ve never had a piece of content go viral. I’ve never been on television. I’ve never been on a billboard. I’m not named brand famous. When you first heard of me, you didn’t know who I was. You had never heard of Dre Baldwin before, did you?

I was familiar with you, but I didn’t know how much you had done. I had heard your name. I’m not a sports person though. I’m not a good person in that realm to ask that question. I met Jerry Rice. I had no idea who he was also. Everybody goes, “That’s Jerry Rice.” I go, “Yes, he was nice. Who was that?”

Jerry Rice is more famous than me.

I have a signed picture from Jerry Rice. I thought he was a nice guy. I don’t deal in the sports world as much. I’d be going, “Have you met Daniel Goleman or somebody who’s an emotional intelligence expert?” That’s my field. You do a lot of things that are similar to what I do. That’s why I was very interested in having you on. People who read this episode like this kind of help. I’m curious what you think is the most valuable thing that people can get from you.

The most valuable thing people can get from me is that no matter what you do, whether you’re an entrepreneur, a doctor, a teacher, a speaker, if you’re a seeker who doesn’t even know what you want to do with your life right now, you’re just trying to figure it out, we all have a “game.” We all are in a game. If you’re an athlete, your game is playing your sport. If you’re a speaker, your game is getting on that stage and giving a speech. Also, a part of your game is getting booked on a stage. If you’re a podcaster, your game is giving that value to your audience. Whatever you’re doing, there’s a game that you’re in. If you do not continue to improve your game, the game is going to pass you by or leave you behind. The better you’re doing in your game, the more visible you need to be. The better you get, the higher a pedestal you’re on, and everybody sees you.

Everybody sees that you’re the one who is winning. You’re the one who is doing your thing. Everybody is coming for you. Everybody is copying what you’re doing. What you’re doing is not going to be innovative six months from now because everybody else is going to be doing the same thing. You must continue to work on your game. With Work On Your Game, I tell people that we target three specific people and three people only. Number one, the person who knows that they don’t have a game, and they need to get better at it. Number two, the person who believes they have a game, but for whatever reason, when it’s time to show it, they are not showing it the way it needs to be seen, or it’s not the people who need to see it. Number three, the person who feels like they are so in their game and they do have it, yet they’re not getting the proper attention. They’re not getting an ROI from the game that they feel like they’re putting out into the world. Those are the three people that we help.

I know that you were doing a free book at Is there any other website or anything else you want to share for people to follow you?

I’m on every platform out there. What I found is if I tell people more than one thing, they forget all of them. We could just stick to That’s where you can get a copy of my free book, The Mirror of Motivation. I’ll ask you that you just cover the shipping. We’ll ship that physical book to you wherever you are. I’m on every other platform. Everybody has social media. They know how to use it. You can look me up on whatever platform you’re on. I’m easy to find. Google me and type in the name of the platform you want, and I’ll be right there.

Dre, this has been so much fun. Thank you so much for being on the show.

I appreciate you having me on, Diane. I’d love to do it again.

I’d like to thank Dre for being my guest. We get so many great guests on this show. If you’ve missed any past episodes, you can go to There’s so much great information on the site about curiosity, perception, and so much more that we talked about on this show. I hope you take some time to look at it. I hope you join us for the next episode of Take The Lead Radio.

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About Dre Baldwin

TTL 806 | Basketball To EntrepreneurshipIn just 5 years, Dre Baldwin went from the end of his high school team’s bench, to the first contract of a 9-year professional basketball career. While playing professional basketball, Dre pioneered new genres of personal branding and entrepreneurship via an ever-growing content publishing empire. Dre started blogging in 2005 and began publishing videos to YouTube in 2006. He has published over 7,000 videos to 134,000+ subscribers, his content being viewed over 73 million times to date. Dre’s daily Work On Your Game Podcast MasterClass has over 1,500 episodes and more than 3 million downloads. Dre has given 4 TED Talks on Discipline, Confidence, Mental Toughness & Personal Initiative and has authored 27 books. He has appeared in national campaigns with Nike, Finish Line, Wendy’s, Gatorade, Buick, Wilson Sports, STASH Investments and DIME magazine.


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